Being Your Own Boss: The Good, the Bad, and the Funny

Photo by sporlab (@sporlab)

Boss's Day rolls around every October, and every year I think the same thing: wait, I need to celebrate myself? That feels a little awkward. But also — kind of wonderful? When you work for yourself, you are the boss. The whole boss. The one who sets the hours, approves the vacation days, and also the one who forgets to take a lunch break for three days in a row.

I noticed something a few years into running my own small creative business. The freedom I thought I was getting was real — genuinely, beautifully real. But it came wrapped in a layer of responsibility I wasn't fully prepared for. Nobody tells you that being your own boss means you also become your own HR department, your own accounting team, and occasionally your own IT support at 11pm when the website does something strange.

The Good

The good parts are the ones that keep you going on the hard days. I think the best thing about working for yourself is that the work actually means something. When I finish a piece or ship an order, it's not just a task checked off a list for someone else's bottom line. It's mine. That feeling doesn't get old.

There's also something to be said for setting your own rhythm. I'm a morning person — always have been. I do my best thinking before 9am with coffee in hand, and I do my worst thinking around 2 in the afternoon when I'd honestly rather be outside. Now I just... work with that instead of against it. That alone has been worth the leap.

And the small joys pile up. Choosing your own music. Wearing what's comfortable. Taking a Tuesday off because the light outside is perfect and you just want to go for a walk. These feel like tiny things, but they add up to a life that fits.

The Bad

Here's the honest part: the bad is real too, and I think it does people a disservice when nobody talks about it.

The loneliness surprised me most. I'm not someone who needs constant company, but working alone day after day — especially in the early years — can get heavy. There's no one to casually debrief with at the end of a hard day. No one who automatically understands what you're dealing with because they're dealing with it too. You have to build that community on purpose, and that takes work.

There's also no one to blame but yourself when things go sideways. That sounds obvious, but living it is different. A bad month, a missed deadline, a product that didn't land the way I hoped — the buck stops with me. That's sobering. I've come to think of it as a grace, actually. It keeps me honest and keeps me growing. But it's not always comfortable.

And the income unpredictability — I won't gloss over that. Some months feel abundant. Others require real faith that the next order is coming. I've learned to hold both without gripping too tight.

The Funny

Now for the part I genuinely love talking about: the absurdity of it all.

I have had full arguments with myself about whether to take a project. Out loud. In my kitchen. I have celebrated a big sale by doing a small, private, completely undignified happy dance that no coworker will ever witness. I have also given myself performance reviews. They were generous.

Being your own boss means you develop a very specific kind of self-talk. Mine ranges from extremely encouraging ("You've got this, you've done harder things") to mildly unhinged ("Why did you agree to that deadline, what were you thinking, who let you make decisions"). Sometimes within the same hour.

I once sent myself a meeting invite so I'd actually sit down and do my bookkeeping. I accepted the meeting. I still almost skipped it.

What I'd Give Myself on Boss's Day

If I'm playing along with the holiday — and I think I will this year — I'd want something that acknowledges the work without being about the work. Something personal and a little beautiful. A piece of art for the space where I create. A mug that makes the morning feel intentional. Something from a small maker who understands what it means to put care into a thing.

That's actually what led me to start making the kinds of pieces I sell in my shop. I wanted things that felt like small celebrations of ordinary, meaningful days. Boss's Day included — even when you are the boss, the employee, and the cleaning crew all at once.

If you're your own boss today, I hope you do something that acknowledges that. Not a grand gesture. Just a moment that says: this work matters, and so do you. You can find a few of my favorite pieces made for exactly that kind of moment over in the shop.

Happy Boss's Day to all of us stubborn, hopeful, slightly sleep-deprived people building something of our own.

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